Rows of jellybean-coloured wooden houses, a fully-operational harbourfront, and streets lined with historical buildings and monuments. This is St. John’s Newfoundland and Labrador, the oldest city in North America, and it is here that I spent several days exploring some of the city’s highlights.

[George Masswohl of George’s Tours St. John’s]
George’s Tours St. John’s offers the unique opportunity to learn about St. John’s history from a passionate guide connected to the Come From Away musical.
With 40 years of acting under his belt, George Masswohl starred as Gander Mayor Claude Elliott in the record-breaking Toronto production of Come From Away, playing to nearly a million people in its two-and-a-half-year run. The musical is based on a true story recalling the events that unfolded in Gander, Newfoundland, after the 9/11 attacks, when 38 planes carrying around 7,000 passengers were diverted to Gander International Airport.
Originally from the Niagara region, George currently lives in St. John’s with his partner Deneen and is passionate about sharing Newfoundland with visitors.
George loves to engage with his tour guests and our afternoon was spent chatting about local culture, music, dining, life in both our respective cities and so much more.
We connected on so many levels that it felt like having a good friend take you around versus a more conventional sightseeing tour.
Stops included Signal Hill, Petty Harbour, Maddox Cove, Cape Spear, Portugal Cove and St. Philip’s, where we indulged in one of the best fish and chips spots in the province at By The Beach. George is like family to the owners and staff there, as he’s brought them a lot of business over the years. Many return to this spot and credit George for the introduction!
His tours offer excellent insight into the fishing industry, Newfoundland’s rich and varied history, plus a wealth of great tips including where to dine in town.

[The Easternmost part of Canada, and sometimes the windiest too!]
Tours are offered in both morning and afternoon. His groups are small (six person max) to allow for a more intimate experience (though he does get larger groups during high season and when cruise ships dock for the day).

[Original Cape Spear Lighthouse, built in 1955]
Dating between circa late 1700’s to the early 1800, the Newman Wine Vaults is one of the oldest standing structures in St. John’s.
Constructed of brick and stone, the Vaults were formerly used to age the celebrated Newman’s Port, brought from Portugal to age here, as well as to a number of other locations around the province. Purely by chance, a vessel laden with port en route from Oporto to London lost its course and wound up spending a winter in St. John’s. Over time, the wine had acquired a new, finer flavour. Due to the province’s cool climate – ideal for maturing port – this turned out to be a lucky accident.
A lucrative trade triangle was formed: Fishing supplies were transported from England to Newfoundland, the vessels sailed back to Portugal filled with cod fish in exchange for the aged wine, then returned to Britain, a major port distributor. This mutually beneficial arrangement lasted for 300 years!
While here, enjoy a wee sample of Newmans Port, right in the heart of the vaults.
Located in the centre of the city on Water Street with an imposing view down to the harbour, the Newfoundland National War Memorial collectively honours all Newfoundlanders and Labradorians who bravely sacrificed their services since World War One.
The Colonial Building served as home to the Newfoundland and Labrador Legislative Assembly from 1850 until 1959. The stately Neoclassical building is a testament to the optimism its builders felt about their future. Beautifully restored, this building is once again a gathering place for people to explore, contemplate, challenge, commemorate, and debate the province’s governance.
I highly recommend a visit to The Rooms, where history, heritage, and artistic expression collide through collections, exhibits, and programs. The Rooms is named after traditional fishing “rooms” – also frequent community gathering spaces – where fisherman and their families would process the daily catch.
The building is modelled after the fishing sheds that can be found around Newfoundland and Labrador. The Art Gallery looks out to the harbour, while the museum points towards the province to reflect both the land and its communities.

[While here, marvel at the Haootia quadriformis on display, a 560-million-year-old fossil!]
Fun fact: Humans have inhabited Newfoundland and Labrador for nearly 9,000 years. The Norse were the first Europeans to settle in this region.

[Badges belonging to 2nd Lieutenant Wilfred Ayre of the Newfoundland Regiment]
Over 12,000 Newfoundland and Labrador men and women served in WW1; many of their stories can be found on the second level. The attention to detail and amount of artifacts is incredible, and anyone with even a bit of WW1 interest will likely spend a good portion of time on this level of The Rooms.
Visitors can also view Royal Newfoundland Regiment and Newfoundland Forestry Corps official military records upon request.
Wesley United Church of Canada is the site of Newfoundland’s first radio broadcast; AM station VOWR still transmits shows from this very location!
Looking for dining recommendations in St. John’s? Some of my faves on Water Street include Rocket Bakery, St. John’s Fish Exchange, and Gingergrass Thai and Vietnamese up on Duckworth Street, for some excellent Pad Thai.
I was hosted by Destination St. John’s for the purpose of this feature. Opinions, as always, remain my own.



































